There are many situations in which a security guard makes rounds when monitoring activity within a building or an exterior location such as a park. In some instances, the security guard may periodically check in while making their rounds. This can involve a guard periodically swiping an access card in a card reader, for example. The security guard may come across a situation that may require additional assistance. In some cases, the security guard may use a phone or walkie-talkie to call for assistance. In some instances, however, there may be a desire for the security guard to be able to quietly call for assistance, for example, without alerting intruders or the like. A need remains for a portable security device that can be carried by a security guard and can quietly, unobtrusively and reliably communicate information and/or solicit assistance. A need also remains for a portable security device that can automatically check-in at predetermined locations while the security guard makes his/her rounds.